Ethyl Acetate → HCID 86634891, compound

HRID 420527Notes

Reaction equation

HRID 420527 reaction equation
Cl[C:2]1[C:3]2[N:4]([C:18]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[CH:19][N:20]=2)[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[C:7]=1[C:8]#[N:9].[N-:27]=[N+:28]=[N-:29].[Na+].CCOC(C)=O>CN(C=O)C>[N:27]([C:2]1[C:3]2[N:4]([C:18]([N:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)=[CH:19][N:20]=2)[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[C:7]=1[C:8]#[N:9])=[N+:28]=[N-:29]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 66658969HCID 66658969, compound

Product 1

HCID 86634891HCID 86634891, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 8-chloro-6-(2,4-dichloro-phenyl)-3-morpholin-4-yl-imidazo[1,2-a]pyridine-7-carbonitrile (135 mg, 0.33 mmol, prepared according to Example 30, Step 16.1) and sodium azide (108 mg, 1.66 mmol) in DMF (1 mL) was heated at 60° C. and stirred for 4 h. The reaction mixture was cooled to RT, poured into AcOEt and washed successively with water and brine. The organic layer was dried over Na2SO4, filtered and evaporated to dryness to yield the crude title compound (144 mg, 0.33 mmol, quant.) as a brownish solid, which was used in the next step without further purification. HPLC: AtRet=2.77.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. washwashed successively with water and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-23b3825c1f4449c8a854aaa1881d9836
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

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